HU198724B - Process for producing thiopyranodi/pyrazole/ derivatives and pharmaceutical compositions comprising same - Google Patents
Process for producing thiopyranodi/pyrazole/ derivatives and pharmaceutical compositions comprising same Download PDFInfo
- Publication number
- HU198724B HU198724B HU88295A HU29588A HU198724B HU 198724 B HU198724 B HU 198724B HU 88295 A HU88295 A HU 88295A HU 29588 A HU29588 A HU 29588A HU 198724 B HU198724 B HU 198724B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- methyl
- preparation
- compound
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 229940124630 bronchodilator Drugs 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 238000005502 peroxidation Methods 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 0 C*N(C(C(C1*)S(C2C)=C)C3=C2N*2C3C2)C(C)(*)*1*=C Chemical compound C*N(C(C(C1*)S(C2C)=C)C3=C2N*2C3C2)C(C)(*)*1*=C 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UPYRWNUARDTVAI-UHFFFAOYSA-N 1-methyl-7h-thiopyrano[3,4-c]pyrazol-4-one Chemical compound C1SCC(=O)C2=C1N(C)N=C2 UPYRWNUARDTVAI-UHFFFAOYSA-N 0.000 description 1
- ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- VOVZEZKGVHTBFB-UHFFFAOYSA-N dihu Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=S)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)OC2C(OC(C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)CO)C(OP(O)(=S)OCC2C(CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=S)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=S)OCC2C(CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=S)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 VOVZEZKGVHTBFB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 210000005092 tracheal tissue Anatomy 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/007,308 US4734431A (en) | 1987-01-27 | 1987-01-27 | Thiopyranodipyrazoles and their use as bronchodilators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT48630A HUT48630A (en) | 1989-06-28 |
| HU198724B true HU198724B (en) | 1989-11-28 |
Family
ID=21725411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU88295A HU198724B (en) | 1987-01-27 | 1988-01-26 | Process for producing thiopyranodi/pyrazole/ derivatives and pharmaceutical compositions comprising same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4734431A (fi) |
| EP (1) | EP0276835B1 (fi) |
| JP (1) | JP2562642B2 (fi) |
| KR (1) | KR960010456B1 (fi) |
| CN (1) | CN1021442C (fi) |
| AT (1) | ATE86999T1 (fi) |
| AU (1) | AU595091B2 (fi) |
| CA (1) | CA1324606C (fi) |
| DE (1) | DE3879235T2 (fi) |
| DK (1) | DK35288A (fi) |
| ES (1) | ES2054711T3 (fi) |
| FI (1) | FI87217C (fi) |
| GR (1) | GR3007404T3 (fi) |
| HU (1) | HU198724B (fi) |
| IE (1) | IE880194L (fi) |
| IL (1) | IL85186A (fi) |
| NO (1) | NO166368C (fi) |
| NZ (1) | NZ223258A (fi) |
| PH (1) | PH24997A (fi) |
| PT (1) | PT86626B (fi) |
| ZA (1) | ZA88528B (fi) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158619A (en) * | 1962-06-14 | 1964-11-24 | Searle & Co | Certain sulfur-containing ortho-fused polycyclic pyrazole derivatives |
| US4042373A (en) * | 1976-06-02 | 1977-08-16 | E. I. Du Pont De Nemours And Company | 2-Aryl-3-chloro-2,4,6,7-tetrahydrothiopyrano[4,3-c]-pyrazoles |
| US4077956A (en) * | 1976-08-30 | 1978-03-07 | E. R. Squibb & Sons, Inc. | 5-Substituted derivatives of dipyrazolo[1,5-a:4',3'-e]pyrazine-6-carboxylic acids and esters |
| US4355164A (en) * | 1981-05-18 | 1982-10-19 | Usv Pharmaceutical Corporation | Pyridothienopyridazine anti-allergy compounds |
-
1987
- 1987-01-27 US US07/007,308 patent/US4734431A/en not_active Expired - Lifetime
-
1988
- 1988-01-21 PH PH36377A patent/PH24997A/en unknown
- 1988-01-21 CA CA000557075A patent/CA1324606C/en not_active Expired - Fee Related
- 1988-01-21 NZ NZ223258A patent/NZ223258A/xx unknown
- 1988-01-22 AU AU10726/88A patent/AU595091B2/en not_active Ceased
- 1988-01-22 FI FI880285A patent/FI87217C/fi not_active IP Right Cessation
- 1988-01-25 IL IL85186A patent/IL85186A/xx unknown
- 1988-01-26 HU HU88295A patent/HU198724B/hu not_active IP Right Cessation
- 1988-01-26 NO NO880340A patent/NO166368C/no unknown
- 1988-01-26 DK DK035288A patent/DK35288A/da not_active Application Discontinuation
- 1988-01-26 ZA ZA88528A patent/ZA88528B/xx unknown
- 1988-01-26 CN CN88100342A patent/CN1021442C/zh not_active Expired - Fee Related
- 1988-01-26 KR KR1019880000563A patent/KR960010456B1/ko not_active IP Right Cessation
- 1988-01-26 PT PT86626A patent/PT86626B/pt not_active IP Right Cessation
- 1988-01-26 IE IE880194A patent/IE880194L/xx unknown
- 1988-01-27 JP JP63014784A patent/JP2562642B2/ja not_active Expired - Fee Related
- 1988-01-27 EP EP88101182A patent/EP0276835B1/en not_active Expired - Lifetime
- 1988-01-27 AT AT88101182T patent/ATE86999T1/de not_active IP Right Cessation
- 1988-01-27 DE DE8888101182T patent/DE3879235T2/de not_active Expired - Fee Related
- 1988-01-27 ES ES88101182T patent/ES2054711T3/es not_active Expired - Lifetime
-
1993
- 1993-03-18 GR GR930400573T patent/GR3007404T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH24997A (en) | 1990-12-26 |
| NO166368C (no) | 1991-07-10 |
| CN88100342A (zh) | 1988-09-14 |
| ES2054711T3 (es) | 1994-08-16 |
| IL85186A0 (en) | 1988-07-31 |
| JP2562642B2 (ja) | 1996-12-11 |
| FI880285A (fi) | 1988-07-28 |
| AU1072688A (en) | 1988-07-28 |
| DK35288D0 (da) | 1988-01-26 |
| CN1021442C (zh) | 1993-06-30 |
| IE880194L (en) | 1988-07-27 |
| PT86626B (pt) | 1991-12-31 |
| DE3879235D1 (en) | 1993-04-22 |
| DE3879235T2 (de) | 1993-06-24 |
| NO166368B (no) | 1991-04-02 |
| FI87217B (fi) | 1992-08-31 |
| CA1324606C (en) | 1993-11-23 |
| JPS63192779A (ja) | 1988-08-10 |
| PT86626A (pt) | 1988-02-01 |
| IL85186A (en) | 1992-02-16 |
| EP0276835A1 (en) | 1988-08-03 |
| EP0276835B1 (en) | 1993-03-17 |
| NO880340D0 (no) | 1988-01-26 |
| HUT48630A (en) | 1989-06-28 |
| FI880285A0 (fi) | 1988-01-22 |
| KR960010456B1 (ko) | 1996-08-01 |
| FI87217C (fi) | 1992-12-10 |
| GR3007404T3 (fi) | 1993-07-30 |
| KR880009028A (ko) | 1988-09-13 |
| NO880340L (no) | 1988-07-28 |
| US4734431A (en) | 1988-03-29 |
| NZ223258A (en) | 1989-11-28 |
| AU595091B2 (en) | 1990-03-22 |
| DK35288A (da) | 1988-07-28 |
| ZA88528B (en) | 1988-09-28 |
| ATE86999T1 (de) | 1993-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |